di-O-adamantoylcurcumin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: di-O-adamantoylcurcumin
• 化学式: C₄₃H₄₈O₈
• 分子量: 692.849
• InChiKey: BWSPCDAWUFHBTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  curcumin 、 金刚烷酰氯 在 sodium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 9.0h， 以47%的产率得到di-O-adamantoylcurcumin
  参考文献：
  名称：

  Synthesis of curcumin and ethylcurcumin bioconjugates as potential antitumor agents

  摘要：

  Some new curcumin and ethylcurcumin bioconjugates with various functionalities supported on the curcumin skeleton were synthesized and evaluated for antitumor activity. Most of the newly synthesized compounds are more active than curcumin and ethyl curcumin but are less cytotoxic than the reference compound doxorubicin. Surprisingly, many of these compounds are not cytotoxic to noncancer cells. Compounds 5c, 5e, 5g, 5j, 6b, and 6g having 5-methylthiadiazole, 6-methoxy-benzothiazole, diethylaminoethyl and the usual alkylating bis(2-chloroethyl)amino moieties showed the highest cytotoxic activity against SK-MEL cancer cells. Compounds 5k, 6c, and 6g are less cytotoxic to KB cancer cells. Moreover, compounds 5c, 5e, 5j, 5k, 6d, 6e, 6f, and 6g showed cytotoxicity against BT-549 cancer cells with 5j being the most active compound. Curcumin and the new intermediate di-O-chloroacetylcurcumin (3a) were also cytotoxic against the same cell line but are less active than the target compounds. Compound 6b is the only one exhibiting cytotoxicity against SK-OV-3 cancer cells.

  DOI：

  10.1007/s00044-011-9587-3

文献信息

• Synthesis of curcumin and ethylcurcumin bioconjugates as potential antitumor agents
  作者：Reem I. Al-Wabli、Omaima M. AboulWafa、Khairia M. Youssef

  DOI：10.1007/s00044-011-9587-3

  日期：2012.6

  Some new curcumin and ethylcurcumin bioconjugates with various functionalities supported on the curcumin skeleton were synthesized and evaluated for antitumor activity. Most of the newly synthesized compounds are more active than curcumin and ethyl curcumin but are less cytotoxic than the reference compound doxorubicin. Surprisingly, many of these compounds are not cytotoxic to noncancer cells. Compounds 5c, 5e, 5g, 5j, 6b, and 6g having 5-methylthiadiazole, 6-methoxy-benzothiazole, diethylaminoethyl and the usual alkylating bis(2-chloroethyl)amino moieties showed the highest cytotoxic activity against SK-MEL cancer cells. Compounds 5k, 6c, and 6g are less cytotoxic to KB cancer cells. Moreover, compounds 5c, 5e, 5j, 5k, 6d, 6e, 6f, and 6g showed cytotoxicity against BT-549 cancer cells with 5j being the most active compound. Curcumin and the new intermediate di-O-chloroacetylcurcumin (3a) were also cytotoxic against the same cell line but are less active than the target compounds. Compound 6b is the only one exhibiting cytotoxicity against SK-OV-3 cancer cells.